You’ve reached one of those moments in parenting that you’ve dreaded: For the second quarter in a row, your son Ethan has come home with poor math grades on his report card. You want to get him the help he needs, so you hire a highly recommended tutor named Zak to help him out. Problem solved, right?

It’s the first week in October. We’re ankle-deep into the school year. The new backpacks, so carefully selected in August, already have a fine patina of crud and some crumpled worksheets or permission slips in more than one compartment. The bright eyed optimism of the back-to-school transition begins to morph to a bleary resignation of another tough day of school ahead.

Let’s face it. In October, it gets real — for students and for parents.

In my first year of college I attended a small, private school in southern New Hampshire. My 18-year-old self was thrilled at the prospect of starting this new adventure. This would be my first experience living away from home, fending for myself, and being completely self-reliant. I could not have been more excited! And, as it turns out, I could not have been more ill-prepared...